Synthesis, anticancer, apoptosis-inducing activities and EGFR and VEGFR2 assay mechanistic studies of 5,5-diphenylimidazolidine-2,4-dione derivatives: Molecular docking studies
Open Access
- 1 July 2019
- journal article
- research article
- Published by Springer Nature in Saudi Pharmaceutical Journal
- Vol. 27 (5) , 682-693
Abstract
A new series of 5,5-diphenylhydantoin derivatives containing benzylidene or isatin (4-19) was synthesized. Their anticancer activity against HeLa, a cervical cancer cell line, A549, a lung cancer cell line, and MDA-MB-231, a breast cancer cell line, was evaluated. Compounds 13, 16, 17 and 18 exhibited potent anticancer activity with average IC50 values against the tested cell lines of 109, 59, 81 and 113 μM, respectively. Compound 16 showed potent EGFR and VEGFR2 inhibitory activity with IC50 values of 6.17 and 0.09 μM, respectively. In addition, compound 16 induced caspase-dependent apoptosis and reactive oxygen species (ROS) production at 5 and 10 μM. Moreover, a molecular docking simulation was performed for compound 16 and sunitinib to predict the protein-ligand interactions with the active site of VEGFR2.Keywords
This publication has 26 references indexed in Scilit:
- Synthesis, antitumour and antioxidant activities of novel α,β-unsaturated ketones and related heterocyclic analogues: EGFR inhibition and molecular modelling studyJournal of Enzyme Inhibition and Medicinal Chemistry, 2018
- Synthesis, anticancer and apoptosis-inducing activities of quinazoline–isatin conjugates: epidermal growth factor receptor-tyrosine kinase assay and molecular docking studiesJournal of Enzyme Inhibition and Medicinal Chemistry, 2017
- Synthesis, anti-inflammatory, analgesic and COX-1/2 inhibition activities of anilides based on 5,5-diphenylimidazolidine-2,4-dione scaffold: Molecular docking studiesEuropean Journal of Medicinal Chemistry, 2016
- Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agentsEuropean Journal of Medicinal Chemistry, 2015
- Synthesis of platinum(II) complexes of isatin thiosemicarbazones derivatives: In vitro anti-cancer and deoxyribose nucleic acid binding activitiesInorganica Chimica Acta, 2014
- Investigation of arenesulfonyl-2-imidazolidinones as potent carbonic anhydrase inhibitorsJournal of Enzyme Inhibition and Medicinal Chemistry, 2014
- Synthesis, single-crystal, in vitro antitumor evaluation and molecular docking of 3-substitued 5,5-diphenylimidazolidine-2,4-dione derivativesMedicinal Chemistry Research, 2013
- Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell lineBioorganic & Medicinal Chemistry Letters, 2013
- 2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agentsEuropean Journal of Medicinal Chemistry, 2013
- Phenytoin-based bivalent ligands: Design, synthesis and anticonvulsant activityArchives of Pharmacal Research, 2012